反应详情

温度

0 °C

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (0.21 g, 1.14 mmol), (2′-methyl-6′-propylbiphenyl-3-yl)methanol (0.25 g, 1.04 mmol) and tributylphosphine (0.39 mL, 1.56 mmol) in tetrahydrofuran (6 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.39 g, 1.56 mmol) with stirring at 0° C., and the mixture was stirred at room temperature for 16 hrs. Diethyl ether was added to the reaction mixture, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1) to give as a colorless oil. This product was then dissolved in a mixed solution of methanol (4.0 mL) and tetrahydrofuran (6.0 mL), 1N aqueous sodium hydroxide solution (2.28 mL) was added at room temperature with stirring, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH 3 with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-1/2) to give the title compound (0.24 g, yield 59%) as colorless crystals. MS (APCI−): 387 (M−H).

1. stirringthe mixture was stirred at room temperature for 16 hrs
2. filtrationthe insoluble material was filtered off
3. concentrationthe filtrate was concentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1)
5. customto give as a colorless oil
6. additionwas added at room temperature
7. stirringwith stirring
8. stirringthe mixture was stirred at room temperature for 1 hr
9. extractionthe mixture was extracted with ethyl acetate
10. washThe organic layer was washed with water and saturated brine
11. dry with materialdried (anhydrous magnesium sulfate)
12. concentrationconcentrated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-1/2)